An Enantioselective β‐Lactam Synthesis Starting from L ‐ (S) ‐Glyceraldehyde Acetonide
1983; Wiley; Volume: 66; Issue: 7 Linguagem: Inglês
10.1002/hlca.19830660732
ISSN1522-2675
AutoresChristian Hubschwerlen, Gerard M. Schmid,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract Complete diastereoselectivity is observed during the cyclocondensation of activated glycine derivatives with aldimines derived from L ‐ (S) ‐glyceraldehyde acetonide. 3,4‐ cis ‐β‐lactams are isolated in high optical and chemical yields. They are converted into key intermediates used in the syntheses of various mono‐ and bicyclic β‐lactam antibiotics. A mechanism is suggested to explain this remarkable diastereoselectivity.
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